4-Methylmorpholine → HCID 68524191, compound

Participants

Reaction Steps

To a solution of 3-{2-[1-(acetylamino)propyl]-4-chlorophenyl}-8-azabicyclo[3.2.1]octane iodide (2-10) (46.8 mg, 0.115 mmol) in dichloromethane (2.0 mL) was added (3R,4R)-1-tert-butyl-3-(2,4-difluorophenyl)piperidine-4-carboxylic acid (1-12) (34.0 mg, 0.115 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′,-tetramethyluronium hexafluorophosphat (HATU, 52.1 mg, 0.138 mmol), 1-hydroxyl-7-azabenzotriazole (HOAT, 19.0 mg, 0.138 mmol), and NMM (35.0 g, 0.345 mmol). The mixture was stirred at room temperature overnight and quenched with a saturated aqueous solution of NaHCO3, extracted with dichloromethane (3×20 mL). The extracts were washed with brine, and dried over anhydrous MgSO4, and concentrated. Purification of the crude residue by prep-TLC (developed with 10% methanol/methylenechloride as mobile phase and separation of isomers by high-pressure liquid chromatography (gradient elution; 15%-95% acetonitrile/water as eluent) and addition of a solution of 1 N HCl solution in ether afforded (2-12) as a white solid (m/z (ES) 600 (MH+)).

Provenance & Evidence